US7728138B2 - Bis-triphenylsilyl compounds and their application on organic electronic device - Google Patents
Bis-triphenylsilyl compounds and their application on organic electronic device Download PDFInfo
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- US7728138B2 US7728138B2 US11/943,282 US94328207A US7728138B2 US 7728138 B2 US7728138 B2 US 7728138B2 US 94328207 A US94328207 A US 94328207A US 7728138 B2 US7728138 B2 US 7728138B2
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- aryl
- substituted
- compound
- bis
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 125000003118 aryl group Chemical group 0.000 claims abstract description 62
- 239000000463 material Substances 0.000 claims abstract description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 230000005525 hole transport Effects 0.000 claims abstract description 11
- 239000010410 layer Substances 0.000 claims description 45
- 125000003277 amino group Chemical group 0.000 claims description 40
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 11
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002560 nitrile group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000010948 rhodium Substances 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 238000005401 electroluminescence Methods 0.000 claims description 9
- 229910052741 iridium Inorganic materials 0.000 claims description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052762 osmium Inorganic materials 0.000 claims description 7
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- 229910052693 Europium Inorganic materials 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- RRBYUSWBLVXTQN-UHFFFAOYSA-N tricyclene Chemical group C12CC3CC2C1(C)C3(C)C RRBYUSWBLVXTQN-UHFFFAOYSA-N 0.000 abstract description 6
- 125000000524 functional group Chemical group 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 0 CCC.[1*]C1=C([Si](C2=CC=CC=C2)(C2=C([6*])C([7*])=C([8*])C([9*])=C2[10*])C2=C([11*])C([12*])=C([13*])C([14*])=C2[15*])C([5*])=C([4*])C([3*])=C1[2*].[16*]C1=C([Si](C2=CC=CC=C2)(C2=C([21*])C([22*])=C([23*])C([24*])=C2[25*])C2=C([26*])C([27*])=C([28*])C([29*])=C2[30*])C([20*])=C([19*])C([18*])=C1[17*].[31*]C.[32*]C Chemical compound CCC.[1*]C1=C([Si](C2=CC=CC=C2)(C2=C([6*])C([7*])=C([8*])C([9*])=C2[10*])C2=C([11*])C([12*])=C([13*])C([14*])=C2[15*])C([5*])=C([4*])C([3*])=C1[2*].[16*]C1=C([Si](C2=CC=CC=C2)(C2=C([21*])C([22*])=C([23*])C([24*])=C2[25*])C2=C([26*])C([27*])=C([28*])C([29*])=C2[30*])C([20*])=C([19*])C([18*])=C1[17*].[31*]C.[32*]C 0.000 description 12
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 6
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- -1 dibromo compound Chemical class 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 150000002503 iridium Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- UUNIOFWUJYBVGQ-UHFFFAOYSA-N 2-amino-4-(3,4-dimethoxyphenyl)-10-fluoro-4,5,6,7-tetrahydrobenzo[1,2]cyclohepta[6,7-d]pyran-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C#N)=C(N)OC2=C1CCCC1=CC=C(F)C=C12 UUNIOFWUJYBVGQ-UHFFFAOYSA-N 0.000 description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 229910000765 intermetallic Inorganic materials 0.000 description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- LNQMQGXHWZCRFZ-UHFFFAOYSA-N triphenyl-[4-(4-triphenylsilylphenyl)phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LNQMQGXHWZCRFZ-UHFFFAOYSA-N 0.000 description 2
- NMLNGEKZNXHJNO-UHFFFAOYSA-N triphenyl-[4-[6-(4-triphenylsilylphenyl)pyridin-2-yl]phenyl]silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1N=C(C=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NMLNGEKZNXHJNO-UHFFFAOYSA-N 0.000 description 2
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
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- 238000001194 electroluminescence spectrum Methods 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
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- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000010458 rotten stone Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
Images
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
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Definitions
- the present invention is generally related to an aromatic conjugated compound, and more particularly to a bis-triphenylsilyl compound and its application on organic electronic devices.
- phosphorescent metal complexes have been used as phosphorescent dopants in an organic light emitting diode.
- these metal complexes used in the light-emitting layer of the organic light emitting diode cyclometalated iridium complexes have been extensively researched since their electron configurations have strong spin-orbit coupling. Since spin-orbit coupling results in mixing between the singlet and triplet excited states, the lifetime of the triplet state is greatly reduced and thereby the phosphorescence efficiency is promoted.
- the doping method can also enhance the efficiency of the device. Therefore, the method of doping phosphorescent substance in a host material is utilized and thus the research 1-3 in blue phosphorescent host materials becomes important.
- developing a novel organic compound having high heat stability and high triplet-state energy to prolong the usage lifetime of the device and to increase luminance efficiency is still an important task for the industry.
- the present invention provides a novel bis-triphenylsilyl compound and its application as a host material, an electron transport material, or a hole transport material in an organic electronic device.
- One object of the present invention is to provide a bis-triphenylsilyl compound having high thermal stability to promote the lifetime of an organic electronic device.
- Another object of the present invention is to provide a bis-triphenylsilyl compound having high triplet-state energy difference, which can not be reached by the general blue phosphorescence host materials, and can be used together with various common phosphorescent materials, such as blue, green, and red phosphorescent materials, like iridium (Ir), platinum (Pt), and osmium (Os) metal complexes. Therefore, this present invention does have the economic advantages for industrial applications.
- the present invention discloses a bis-triphenylsilyl compound.
- the bis-triphenylsilyl compound has the following general structure:
- G represents any atomic moiety or single bond of the functional group selected from the group consisting of the following: aryl group, cyclene group, and heterocyclic ring group; and R 1 ⁇ R 32 represent substituents on aryl groups.
- the invention also discloses the application of the bis-triphenylsilyl compound, especially the application as a light-emitting host material, an electron transport material, or a hole transport material in an organic electroluminescence device or phosphorescence device; or the application as an electron transport material or a hole transport material in other organic electronic devices.
- FIG. 1 shows a structural schematic diagram illustrating a multi-layer organic light emitting device according to the invention
- FIGS. 2 ⁇ 8 show absorption and emission spectra of examples 2 ⁇ 8, respectively;
- FIG. 9 shows electroluminescence and CIE coordinate diagram of the device E
- FIG. 10 is a diagram showing the dependence of candela and current density versus voltage
- FIG. 11 shows electroluminescence and CIE coordinate diagram of the device F.
- FIG. 12 is a diagram showing the dependence of candela and current density versus voltage for the device F.
- the bis-triphenylsilyl compound has the following general structure:
- the above G represents any atomic moiety or single bond of aryl group, cyclene group, or heterocyclic ring group.
- G represents a single bond, in the above mentioned structure, aryl groups on the two sides of G is bonded with one single bond.
- the aryl group, cyclene group, or heterocyclic ring group each can comprise at least one substituent.
- the substituent is selected from the group consisting of the following: H atom, halogen atom (such as F, Cl, Br, I); aryl group; halogen substituted aryl group; C1-C20 haloalkyl substituted aryl group; C1-C20 haloalkyl substituted aralkyl group; aryl substituted C1-C20 alkyl group; C1-C20 alkyl group, C1-C20 cycloalkyl group (such as methyl, ethyl, butyl, cyclohexyl); C1-C20 alkoxy group; amino group; aryl substituted amino group; C1-C20 alkyl substituted amino group; nitrile group; nitro group; carbonyl group; cyano group (—CN); substituted aromatic amino group; aryl phosphoryl (P ⁇ O) group; Si-containing aryl group; and heterocyclic ring group.
- halogen atom such as F, Cl, Br
- R 1 ⁇ R 32 can be identical or different and R 1 ⁇ R 32 are independently selected from the group consisting of the following: H atom, halogen atom (such as F, Cl, Br, I); aryl group; halogen substituted aryl group; C1-C20 haloalkyl substituted aryl group; aralkyl group; C1-C20 haloalkyl substituted aralkyl group; aryl substituted C1-C20 alkyl group; C1-C20 alkyl group, C1-C20 cycloalkyl group (such as methyl, ethyl, butyl, cyclohexyl); C1-C20 alkoxy group; amino group; aryl substituted amino group; C1-C20 alkyl substituted amino group; nitrile group; nitro group; carbonyl group; cyano group (—CN); substituted aromatic amino group; aryl phosphoryl (P ⁇ O) group; Si-containing aryl
- the aryl group comprises phenyl, naphthyl, diphenyl, anthryl, pyrenyl, phenanthryl, fluorene, or other multi-phenyl group.
- the heterocyclic ring group can be pyrane, pyrroline, furan, benzofuran, thiophene, benzothiophene, pyridine, quinoline, isoquinoline, pyrazine, pyrimidine, pyrrole, pyrazole, imidazole, indole, thiazole, isothiazole, oxazole, isoxazole, benzothiazole, benzoxazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetraazole, phenanthroline, or other heterocyclic aryl group.
- the compound D-03(10 mmole) is dissolved in 40 mL of THF (tetrahydrofuran).
- THF tetrahydrofuran
- n-butyl lithium (10 mmole) is gradually added and the reaction is carried out for 30 minutes to form an organic lithium reagent.
- trimethyl borate (10 mmole) is added.
- the temperature of the reaction flask is gradually returned to room temperature.
- 10% hydrochloric acid solution is added and extraction by ethyl acetate is carried out.
- the organic layer is treated with anhydrous magnesium sulfate to remove water content and then the solvent in the organic layer is removed by a rotary evaporator.
- the compound B-08 (10 mmol), dibromo compound or D-03 (5 mmol), and Pd(PPh 3 ) 4 (0.2 mmole) are dissolved in 50 mL of deoxygenated toluene, 4 mL of ethanol, and 10 mL of 2M potassium carbonate solution.
- the mixture is heated to 80° C. and the reaction is carried out for 24 hrs.
- 50 mL of ethyl acetate is added.
- the organic layer is filtered by tripoli and is treated with anhydrous magnesium sulfate to remove water content.
- the solvent in the organic layer is removed to obtain solids.
- the solids are sequentially washed by distilled water, methanol, and ether.
- the bis-triphenylsilyl compound is obtained.
- the bis-triphenylsilyl compound has excellent heat stability and high triplet-state energy difference. Therefore, as the bis-triphenylsilyl compound is applied in an organic electronic device, the excellent heat stability makes the lifetime of the organic electronic device increased.
- the bis-triphenylsilyl compound has high triplet-state energy difference, which can not be provided by the existing known blue phosphorescence host materials, and can be used together with various common phosphorescent materials, such as blue, green, and red phosphorescent materials, like iridium (Ir), platinum (Pt), osmium (Os), copper (Cu), rhodium (Rh), europium (Eu), and ruthenium (Ru) metal complexes.
- Ir iridium
- Pt platinum
- Os osmium
- Cu copper
- Rhodium Rh
- Eu europium
- Ru ruthenium
- the wavelength irradiated from the light-emitting layer can be adjusted according to actual needs.
- various common phosphorescent materials such as blue, green, and red phosphorescent materials, like iridium (Ir), platinum (Pt), osmium (Os), copper (Cu), rhodium (Rh), europium (Eu), and ruthenium (Ru) metal complexes
- Ir iridium
- platinum platinum
- Os osmium
- Cu copper
- Eu europium
- Ru ruthenium
- the bis-triphenylsilyl compound can be applied in an organic electroluminescence and/or phosphorescence device, especially used as a host material, an electron transport material, or a hole transport material.
- the bis-triphenylsilyl compound can also be applied as an electron transport material or a hole transport material in other organic electronic device.
- the organic electronic device can be a solar cell, an organic thin film transistor, an organic photoconductor, or other organic semiconducting device well-known to those who are skilled in the art.
- an organic light emitting device is disclosed.
- the color of light emitted by the organic light emitting device is determined by the fluorescent organic material in the device. Therefore, by doping small amount of guest emitters with high luminance efficiency in host emitters, the recombination efficiency of carriers can be increased. These guest emitters have smaller energy gap, higher luminance efficiency, and shorter recombination lifetime than the host emitters. Therefore, the excitons of the host emitters quickly transfer to the guest emitters through energy transition to carry out recombination effectively. Besides increasing luminance efficiency, the color of the emitted light covers the whole visible light region.
- guest emitters are used together with host emitters by co-evaporation or dispersion, or by spin coating.
- Guest emitters receive energy from the excited host emitters through energy transfer or carrier trap to produce different colors, such as red, green, and blue, and to increase luminance efficiency.
- fluorescence guest emitters new development in phosphorescence material is also researched. As an organic molecule is excited, one quarter of excited electrons form asymmetric spin siglet state and release energy through fluorescence. However, three quarters of excited electrons form symmetric spin triplet state but do not release energy through radiated phosphorescence to thereby lose efficiency.
- the material capable of releasing the triplet-state energy of the excited electrons through radiated phosphorescence usually is an organic metallic compound having a center transition metal, such as osmium (Os), iridium (Ir), platium (Pt), europium (Eu), ruthenium (Ru), etc., and the ligand of the organic metallic compound is a nitrogen-containing heterocyclic compound.
- the organic light emitting device comprises a pair of electrodes and at least one organic layer provided between the electrodes.
- the at least one organic layer comprises one light-emitting layer and at least one of the organic layers comprises one bis-triphenylsilyl compound, having the following general structure:
- G represents any atomic moiety or single bond of aryl group, cyclene group, or heterocyclic ring group.
- G represents a single bond, in the above mentioned structure, aryl groups on the two sides of G is bonded with one single bond.
- the aryl group, cyclene group, or heterocyclic ring group each can further comprise a substituent.
- the substituent is selected from the group consisting of the following: H atom, halogen atom (such as F, Cl, Br, I); aryl group; halogen substituted aryl group; C1-C20 haloalkyl substituted aryl group; aralkyl group; C1-C20 haloalkyl substituted aralkyl group; aryl substituted C1-C20 alkyl group; C1-C20 alkyl group, C1-C20 cycloalkyl group (such as methyl, ethyl, butyl, cyclohexyl); C1-C20 alkoxy group; amino group; aryl substituted amino group; C1-C20 alkyl substituted amino group; nitrile group; nitro group; carbonyl group; cyano group (—CN); substituted aromatic amino group; aryl phosphoryl (P ⁇ O) group, Si-containing aryl group; and heterocyclic ring group.
- halogen atom
- R 1 ⁇ R 32 can be identical or different and R 1 ⁇ R 32 are independently selected from the group consisting of the following: H atom, halogen atom (such as F, Cl, Br, I); aryl group; halogen substituted aryl group; C1-C20 haloalkyl substituted aryl group; C1-C20 haloalkyl substituted aralkyl group; aryl substituted C1-C20 alkyl group; C1-C20 alkyl group, C1-C20 cycloalkyl group (such as methyl, ethyl, butyl, cyclohexyl); C1-C20 alkoxy group; amino group; aryl substituted amino group; C1-C20 alkyl substituted amino group; nitrile group; nitro group; carbonyl group; cyano group (—CN); substituted aromatic amino group; aryl phosphoryl (P ⁇ O) group; Si-containing aryl group; and heterocyclic atom
- the aryl group comprises phenyl, naphthyl, diphenyl, anthryl, pyrenyl, phenanthryl, fluorene, or other multi-phenyl group.
- the heterocyclic ring group can be pyrane, pyrroline, furan, benzofuran, thiophene, benzothiophene, pyridine, quinoline, isoquinoline, pyrazine, pyrimidine, pyrrole, pyrazole, imidazole, indole, thiazole, isothiazole, oxazole, isoxazole, benzothiazole, benzoxazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetraazole, phenanthroline, or other heterocyclic aryl group.
- the bis-triphenylsilyl compound structure is applied in the light-emitting layer of the organic light emitting device.
- the bis-triphenylsilyl compound structure is applied as a host material in the light-emitting layer of the organic light emitting device.
- the light-emitting layer can further comprise a guest emitting material and the guest emitting material comprises a transition metal complex.
- the transition metal of the transition metal complex can be selected from the group consisting of the following: iridium (Ir), platinum (Pt), osmium (Os), copper (Cu), rhodium (Rh), europium (Eu), and ruthenium (Ru).
- the guest emitting material can be a blue, green, or red phosphorescence material.
- the bis-triphenylsilyl compound structure can be applied in a hole transport layer of the organic light emitting device.
- the bis-triphenylsilyl compound can be applied in an electron transport layer of the organic light emitting device.
- a glass substrate is used.
- a positive electrode, a hole-injection layer (can be omitted), a hole-transporting layer, a light-emitting layer, a hole-blocking layer (can be omitted), an electron-transporting layer, an electron-injection layer (LiF) (can be omitted), and a negative electrode are sequentially formed on the substrate.
- the positive electrode is conductive indium-tin-oxide (ITO) and has a thickness of 100 nm.
- the light emitting layer is formed by doping phosphorescent material as the guest emitter in the host emitter. Before the evaporation of the organic layers, the ITO glass is cleaned by the purchased cleanser and organic solvent and finally is treated by a UV-ozone cleaner.
- FIG. 1 shows a structural schematic diagram illustrating a multi-layer organic light emitting device according to the invention, where the actual thickness of each layer is not related to the drawn dimension in the figure.
- the layer structure of the organic light emitting device comprises a substrate 100 , a positive electrode (+), a hole-injection layer 10 , a hole-transporting layer 20 , an electron-blocking layer (not shown in the figure), an emitter (light-emitting layer) 30 , a hole-blocking layer 40 , an electron-transporting layer 50 , and a negative electrode ( ⁇ ).
- the electron-blocking layer, hole-blocking layer 40 , and hole-injection layer 10 can be existed or omitted, depending on the requirement of the device.
- the components between the positive and negative electrodes form the electroluminescent medium 400 .
- the emitter (light-emitting layer) 30 is formed by doping phosphorescent material as the dopant in the host compound.
- the OLED device is fabricated, the EL spectra and CIE coordination of the device are measured by Hitachi F-4500 spectra scan spectrometer.
- the properties, such as current, voltage, and brightness of the device are measured by Kiethley 2400 programmable voltage-current source. The measurements are carried out at room temperature (about 25° C.) and 1 atm.
- the material for the hole-injection layer in the OLED can be CuPc, m-MTDATA, and 2-TNATA shown in the following structure group G1.
- the material for the hole-transporting layer in the OLED can be NPB, TPD, NCB, PPB, TCTA, MPMP, and HMTPD shown in the following structure group G2 or other aniline compound.
- the material for the hole-blocking layer in the OLED can be TPBI shown in the following structure group G3 or BCP, BAlq, PAlq, and SAlq shown in the following structure group G4.
- the material for the electron-transporting layer in the OLED can be TPBI, TAZ-1, TAZ-2, TAZ-3, and PBD shown in the above structure group G3 or Alq 3 or DPA shown in the following structure group G4.
- the guest emitting material (dopant) used in the OLED can be FIrpic, FIrpytz, FIrN 4 , FIr 6 , and Ir(pmb) 3 shown in the following structure group G5.
- the material for the electron-blocking layer in the OLED can be CBP, CCP, mCP, and TCB shown in the following structure group G6.
- the pressure in the chamber is about smaller than 5 ⁇ 10 ⁇ 6 torr during evaporating organic compounds, phosphorescent iridium complexes, and metals.
- the evaporation rate for the organic films is controlled at about 1.5 ⁇ 2.5 ⁇ /s while the evaporation rate for the phosphorescent iridium complexes is controlled at about 0.05 ⁇ 0.2 ⁇ /s.
- the evaporation rate for LiF is about 0.5 ⁇ /s.
- the thickness of the hole-injection layer is about 10 ⁇ 15 nm.
- the thickness of the hole-transporting layer is about 25 ⁇ 50 nm.
- the thickness of the hole-blocking layer is about 10 ⁇ 20 nm.
- the thickness of the electron-transporting layer is about 10 ⁇ 50 nm.
- the thickness of the electron-injection layer (LiF) is about 0.1 nm.
- the negative electrode is Mg—Ag alloy or aluminum.
- the Mg/Ag co-evaporation with a ratio of 10:1 is carried out to form a film with a thickness of 55 nm.
- a silver layer having a thickness of about 100 ⁇ 150 nm as a protection layer is formed.
- the evaporation rate for aluminum is about 3 ⁇ /s and the thickness is about 100 ⁇ 150 nm.
- the bis-triphenylsilyl compound according to the invention can be used as the phosphorescent host material in the organic light emitting diode and the fabricated device emits blue phosphorescence. Furthermore, the device has high brightness, high current efficiency, and excellent CIE coordinate and thus is valuable for industrial applications.
- the bis-triphenylsilyl compound is applied as a host material in an organic electroluminescence device.
- the bis-triphenylsilyl compound has the characteristics of electron and hole transport to be applied as an electron transport material or a hole transport material in other electronic devices, besides in an organic electroluminescence device.
- the bis-triphenylsilyl compound has the excellent heat stability to make the lifetime of the organic electronic device effectively increased.
- the bis-triphenylsilyl compound has high triplet-state energy difference.
- the bis-triphenylsilyl compound provides high triplet-state energy difference, which can not be provided by various common blue, green, red phosphorescent host materials, and can be used together with various common phosphorescent materials, such as the iridium (Ir), platinum (Pt), osmium (Os), copper (Cu), rhodium (Rh), europium (Eu), and ruthenium (Ru) metal complexes. Therefore, this invention does have the economic advantages for industrial applications.
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Abstract
Description
where G represents any atomic moiety or single bond of the functional group selected from the group consisting of the following: aryl group, cyclene group, and heterocyclic ring group; and R1˜R32 represent substituents on aryl groups.
At first, as shown in Scheme 1, p-dibromobenzene (10 mmole) is placed in a reaction flask and dissolved in 40 ml of ether. After the reaction flask is cooled to −78° C., n-butyl lithium (10 mmole) is gradually added into the reaction flask to form a lithium reagent. Separately, triphenylsilyl chloride (10 mmole) is dissolved in 40 ml of ether. After cooled to −78° C., this ether solution is added into the reaction flask that contains the lithium reagent. At −78° C., the reaction is carried out for 3 hrs. Then, the temperature of the reaction flask is returned to room temperature. The reaction is carried out for 1 hr at room temperature. After the reaction is finished, 4N hydrochloric acid solution is added. The suction filtration is used to separate solids. White solids D-03 are obtained [1H NMR (400 MHz, CDCl3): δ 7.51-7.53 (m, 6H), 7.49-7.50 (m, 2H), 7.35-7.44 (m, 11H)].
- Device A: TCTA (30)/mCP(20)/FIrpytz:BSB (6%)(30)/BCP (10)/Alq (30)/Mg:Ag
- Device B: TCTA (30)/mCP(20)/FIrpytz:pBST (6%)(30)/BCP (10)/Alq (30)/Mg:Ag
- Device C: TCTA (30)/mCP(20)/FIrpytz:mBST (6%)(30)/BCP (10)/Alq (30)/Mg:Ag
- Device D: TCTA (30)/mCP(20)/FIrpytz:mBSP (6%)(30)/BCP (10)/Alq (30)/Mg:Ag
- Device E: TCTA (30)/mCP(20)/FIrpytz:oBST (6%)(30)/BCP (10)/Alq (30)/Mg:Ag
- Device F: NPB (30)/mCP(20)/FIrpytz:mBST-F (6%)(30)/TPBI (30)/LiF(1)/Al
TABLE 1 | ||||||
Maximum | ||||||
Thresh | external | Maximum | Maximum | CIE | Maximum | |
old | quantum | brightness | efficiency | coordinate | emitting | |
voltage | efficiency (%) | (cd/m2) | (cd/A) | (8 V) | wavelength | |
device | (V) | (voltage/Volt) | (voltage/Volt) | (voltage/Volt) | (x, y) | (nm) |
A | 6.0 | 12.53 (11.5) | 22054 (16.0) | 22.70 (11.5) | 0.13, 0.25 | 462 |
B | 5.3 | 1.88 (7.5) | 4863 (17.0) | 3.38 (7.5) | 0.15, 0.28 | 472 |
C | 5.4 | 8.64 (10.5) | 15133 (15.0) | 14.47 (10.5) | 0.13, 0.24 | 462 |
D | 6.7 | 9.16 (13.0) | 15256 (18.0) | 18.8 (13.0) | 0.15, 0.30 | 462 |
E | 4.8 | 10.40 (8.5) | 14203 (14.0) | 17.73 (8.5) | 0.13, 0.23 | 462 |
F | 6.6 | 10.17 (10.0) | 9014 (15.5) | 15.08 (10.0) | 0.13, 0.21 | 462 |
Claims (19)
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